Reacción #9549

Ecuación de reacción

7-bromo-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline

3-Chloroperoxybenzoic acid

ammonium hydroxide

p-toluenesulfonyl chloride

→

7-bromo-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe crude product was obtained as an oil, which
2. 2
   Otroto form a precipitate
3. 3
   OtroThe precipitate was isolated by filtration
4. 4
   Lavadowashed with a small amount of acetonitrile
5. 5
   Otrorecrystallized from acetonitrile

Procedimiento

The method described in Part J of Example 365 was used to oxidize and aminate 7-bromo-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline (18.7 g, 58.4 mmol). 3-Chloroperoxybenzoic acid (22.1 g of 50% pure material, 129 mmol) was added in five portions during the oxidation step, and the amination with ammonium hydroxide (146 mL) and p-toluenesulfonyl chloride (16.6 g, 87.6 mmol) proceeded overnight. The crude product was obtained as an oil, which was treated with acetonitrile to form a precipitate. The precipitate was isolated by filtration, washed with a small amount of acetonitrile, and recrystallized from acetonitrile to provide 4 g of 7-bromo-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine as off-white needeles, mp 218–220° C.

Fuente